


Con's Kinda Bet

by NihilismPastry



Series: Commissions [8]
Category: Undertale (Video Game)
Genre: Choking, F/M, Mafiafell Au, Pet Play, Rough Sex
Language: English
Status: Completed
Published: 2017-09-07
Updated: 2017-09-07
Packaged: 2018-12-24 23:24:06
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,541
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/12023247
Author URL: https://archiveofourown.org/users/NihilismPastry/pseuds/NihilismPastry
Summary: Sans makes a bet that he can get a singer to become a whore.





	Con's Kinda Bet

**Author's Note:**

> Kinks: Choking, pet play, rough sex
> 
> AU: Mafiafell
> 
> Reader Type: Female

She swung her hips in time with the band, her singing soft and low, but still managing to catch the attention of every single person in the old, greasy speakeasy. She had one of those sweet voices that wasn’t roughed up from excessive use of cigarettes and downing enough gin and tonic to make the local drunk tell her it’s enough. But it wasn’t the sweet pipes she had that really kept all those eyes on her, instead it was her pretty looks. In the light of the cracked chandelier, with the light scattering across her face, and that tasteful dress on her body, she looked like she just stepped out of one of those sinful French magazines. As the song ended, and the audience began to clap, she made a sweet curtsey, before sashaying off stage and to the bartender. She was a slim spider Monster, with six eyes, a charming smile, and more than enough hit men under her belt to make even Al Capone nervous.

He brought the cigar to his teeth and inhaled, red smoke curling out of his sockets, making the human next to him shudder. “Ah, ya know this place kinda banned smoking, right?”

“lil’ miss muffet and i go way back.” Sans said, though he extinguished the cigar anyway. The butt was left with a pile of others in a silver ashtray next to a bottle of beer. “ya got the plans for the whore house?”

The man scrambled for a suitcase off to the side, and dragged it up, he cracked it open and fiddled around for a few minutes, before pulling out a file thick with papers. He passed it over to Sans who began leafing through them, crimson eye lights taking them in. There were scribbles in the margins, sketches of the building itself, and even some basic designs for an interior. Whore houses, while illegal, would bring in all sorts of business that the Grave family desperately needed right now. Monsters had only been on the surface for the last three years, playing the crime game for two. Proving himself to be a good Don was always a troublesome task, but owning a speakeasy that was also a whore house? Quite the den of sin that hadn’t been breached yet.

Humans weren’t any fun.

Those sin dens were a dime a dozen in the Underground, and Sans was certainly happy to make one. His gaze lifted from the papers, and back on the human, who was sipping a glass of water. He watched the provocative sway of her hips, and the way her hand fluttered as she talked up Muffet, who was regarding her with a blank look. He was too far away to hear the conversation, but whatever it was, had a smile on the canary’s face. “ya got any dolls lined up to work yet?”

The human paused, his glass to his lips. “Uh, not yet. I mean construction is almost done and all, so I guess we should get on it, but we haven’t had any good connections yet.” He set down his now warm whiskey. “Did you have anyone in mind? Polly Baker has been getting a lot of business recently,” His face went warm, he probably knew from personal experience. “And then there’s Susan Chang. And-”

“get me some new blood.” He said. “not some sloppy toss outs with loose cunts. lopez’s girls can go fuck themselves.”

“Sir, you can’t just ask someone if they want to be a whore…” 

“Oh?” A light voice said, it had hint of an accent to it. A rugged old man walked up to the table, his green eyes looking Sans and his assistant over. “I didn’t know Sans Graves was still kickin’ about. Though old man Lopez kicked you to the side by now.”

Sans dug a hand into his pocket, taking out another cigar. “Yup, but I don’t need to make deals with dead men.”

“That’s quite the boast.” He went over to a chair opposite him, and sat down. “And what would you be working on that would cut out the most influential man in this god forsaken city?”

Sans glanced over to the other human, who was now sipping at his whiskey. Seeing as how he got no help on that front, he looked to the old man again, waving some of the papers. “whore house. gotta feed this city sex and cum, am i right?”

“And you don’t intend to use Lopez’s women?”

“nope.”

The old man gave a wet laugh, before it dissolved into a cough. “Fresh meat is hard to come by. You’ll never do this without my employer’s help, you know.”

“i’ll tell ya what,” Sans put the cigar between his teeth, magic causing it to heat up and burn. “i snag muffet’s canary, get her to sign, and ya owe me $10,000 grand.”

The old man shifted in his chair, taking in the pretty singer from earlier. “get her to sign tonight, i’ll pay double.”

Sans’ grin stretched and he slapped a sheet of paper down. He yanked the pen from his assistants ear, earning a whine in protest, and began jotting something down. He signed his name in that stupid font, before sliding it over to the old man. “well james, it’s gonna be the bet of the ages, don’t ya think?”

The old man took the pen, and signed his first name. “I’d say I wouldn’t bet my money on it, but seeing as how I am…” He handed back the pen and paper. “Maybe that luck of yours will finally dry up.”

“my luck ain’t like your dick.”

James pushed himself up from the chair, shaking his head. “I’ll be back for my money, Sans.”

* * *

You sighed and sipped at the cool water Muffet had given you. It was a hot summer’s night, and it was made even hotter thanks to the massive crowd that had poured into the spider Monster’s speakeasy. They were looking for a cool drink and a good time, two things that could be gotten for the right price. You, meanwhile, simply wanted to pay for the rent this month, so you made your rounds at the local bars, singing with any band that was willing to have you. Muffet’s band normally asked you back, so this was the place you haunted the most. It had a nice mix of folks, Monsters and humans, and the pay wasn’t too bad either. Despite the spider Monster’s reputation, she payed pretty decently.

You sighed and leaned heavily against the wooden bar top. “Muffet, please tell me you have some of those rolls hidden in one of your sleeves.”

“You know I don’t serve food.” She said with a wave of one hand, the other five serving drinks to a gaggle of young humans. “It brings all the wrong people to my door. I just need drunks, not high life people who want a bite to eat with a glass of wine.” Two of her eyes narrowed. “They don’t pay as well as the drunks. If you’re hungry, bring your own food next time.”

“I did last time, and it was stolen!”

“Then go to the diner across the street.”

“I work at a diner during the day.” Your nose wrinkled at the thought. “I basically live off eggs, coffee, and bacon.”

“That’s my problem, how?” The woman put the drinks in front of the humans, and they took them, leaving the bar more or less clear now. “Well you could always get food from-” Muffet’s eyebrows furrowed and she crossed all three pairs of her arms. “Good evening, Sans.”

You felt a shiver go down your spine, and you carefully peered behind you. Standing there, hands stuffed in his pockets, was none other than Sans Graves. He was one of only two skeleton Monsters that haunted the city, and was always described as sharp fanged and sharp witted. He was smaller than you thought he’d be, but as he sauntered up to you, that cigar bobbing from his fangs, and those red eyes looking you up and down, you knew he didn’t need his brother’s famed height to make him scary.

You began to move away, but he shook his head and sat in the bar stool next to your own. “now why would this beautiful lady try runnin’ away, hm? got a date with one of the buddin’ alcoholics?”

“N-no, I just um…” You shifted from one leg to another. “I needed to go powder my nose.”

“pretty doll like you?” He scoffed, and took the cigar from between his teeth. It was now that you noticed he didn’t need to open his mouth to talk. “don’t need all them creams and powders. ya look good enough to eat.”

“...”

Muffet rolled her eyes. “What’ll it be Sans? I mean, outside my singer’s patience.”

“i’d like to have a chat with her in private.” He said. “if that would be alright with the doll.”

You shot a glance top Muffet, but she shrugged, not caring in the slightest. You should’ve known, so long as no one interrupted her work, then she didn’t care what went down. That was why there were ‘ladies of the night’ selling themselves in a corner, a few men gambling away their pay next to the stage, and a man covered in blood was nursing a glass of sherry. Sans Graves wanting to speak to you ‘in private’ was hardly worth any of her time or energy.

Which was how you found yourself sitting in a back room, on a small couch, staring up at a pacing mafia boss. He had a new cigar between his fangs, the other dumped into a glass of water you had brought with you. The skeleton suddenly paused and turned to stare at you, his red eye lights fixated on your face. “how’s the pay tiny tits is given’ ya?”

“Tiny tits?” You shook your head. “Look, I’ve already had people from the different mobs approach me on being a spy, and it just doesn’t appeal to me. I-”

“not what i was goin’ for, doll.” He said, cutting her off with a thoughtful look. “ambitious, sure. but that ain’t what i dragged ya in here for.” He walked over to her, hands still stuffed in his pockets. “i have a proposition for ya. a real money maker, if ya want it.”

Money?

“I’m listening.”

His grin turned up at the edges. “thought ya might wanna hear it.” He went over to the couch and sat down. “long story short, i’ll be opening up a brothel and speakeasy. same building, same place sorta deal. i got the booze, got the muscle, just need some pretty call girls such as yourself.”

“You want me to be a whore?”

“i’m wantin’ ya to be a star.” He corrected. “just sing a few of your songs, and let somebody show ya a good time at the end of the night. just one, and you’ll get fifty percent of the profits from your romp, one hundred percent from your croonin'.”

“How much are you paying?”

He took a pen out of his vest pocket and took your hand, and wrote something down. Your eyes widened and you bit your lip. That was far more than all the singing you did in a month, maybe in two months. That could get you out of your tiny apartment on the west side, and get you something further from the railroad tracks. You wouldn’t have to feel your walls and floor shake every few hours, you wouldn’t have to listen to the train go by every night, and you could even get a new bed.

“And what do you want out of it, outside my money?”

“just need a lil interview.” He said. “gotta make sure you’re good enough for the job. Know you got a good pair of pipes, but what ‘bout this body of yours.” His eye lights trailed up and down body. Suddenly your dress felt so very revealing, and you had the urge to cover your chest. “is it right for the job.”

He reached out with his thin fingers tracing your arm, before looping one around the strap of your dress and tugging. The cheap fabric ripped under his strength, and you felt a shiver go down your spine as he moved the torn fabric out of the way, revealing more of your soft skin. “Here in this speakeasy? Don’t you have money for a motel or-”

He pressed his teeth to your lips, and ripped the rest of the dress away. You could feel the spark of something on your lips. It ignited something deep inside of you, and without you noticing, you moved closer to him. His fingers trailed up from your clavicle, letting go of the torn fabric, revealing your breasts to him. “nothin’ underneath, what a naughty girl.” His fingers curled around your neck and squeezed. “maybe i should punish you for that, hm?”

He pushed you back into the couch, and pulled your dress down the rest of the way, and tossed it onto the floor. His teeth  was on your mouth again, that buzzing still there, causing a low moan to bubble in your throat. His fingers squeezed a bit harder at the sound. “nuh uh, good bitches get to talk when their master says they can.”

He pulled away from you entirely, and began loosening his belt. You weren’t sure what you were expecting a skeleton to have, but you were surprised to see a red, glowing dick spring from his slacks. You didn’t get much of a chance to actually look at it, as he crawled onto your stomach, and stuffed it into your mouth. His fingers tangled in your hair, and he bucked his hips, forcing the dick to slide deeper. “now, way i see it, if ya can make me cum before you do, i’ll let my little puppy get her reward, ya want that?”

You whimpered around his length, earning a low moan in response. You quickly began sucking at his tip, using your tongue to massage the underside of his dick the best you could from this position. Meanwhile, you could feel his cold fingers creeping down your thighs, scratching here and there, until they finally made it to your cunt. He chuckled as he speared a finger into it, swirling around the juices. “look, bitch is already wet from just this. like suckin’ monster cock, huh?”

He began fingering you at a rapid pace, stuffing as many fingers into you as your pussy could hold, and watching you nearly choke on his dick as he bucked his hips into your awaiting mouth. It didn’t take long for your orgasm to begin pricking at your senses, making your toes curl, and causing your legs to shake. You pushed yourself onto your forearms, and swallowed as much of the skeleton’s dick as possible, even humming to try and bring him closer to orgasm. However, it was all for naught as you felt that coil snap, and your back arch, pleasure flooding your every pore as you finally hit that point.

The skeleton had no pity on you though, using your mouth as a cock sleeve, and still pumping his fingers into your pussy. You could hear him above you, calling you bad pet, praising the slutty look on your face, asking if it was worth it. Soon the pleasure began to borderline pain as you edged away from pleasure, and into over stimulation. “come on pup,almost there. let master cum on that pretty face of yours.”

You shut your eyes as the dick was slid out of your mouth with a lewd pop, and you could hear him moan your name as he fucked himself. When you opened your eyes again, you moaned as fingers were ripped out of your pussy, but also from his expression. His tongue hung from his mouth, his stare intense as his chest seemed to expand and contract like he was breathing. Suddenly something hot spurt onto your cheek, and it was was quickly followed by another. You raised up a hand, and spread some of the cum on your finger, before licking it away. Sans hissed as he watched, but didn’t move. “ya like that?”

“Spicy, a little thick.” You licked your lips. "Not bad though."

“you’d get it every night, even better if ya worked for me.”

You licked away more cum, wriggling on the couch. Your jaw and pussy was sore, and you were worried the bright red would stain all over your face. But as you stared up at the grinning skeleton, you knew you’d likely never get a better opportunity in your life. “Okay, I’ll be your whore.”

You were surprised to find a pen and paper pushed into your hands. He tapped a cum slick finger on a dotted line. “right there.”

You gave your signature, and the ink hadn’t even dried before the paper and pen were snatched from you, and stuffed into his pants. He grinned and dug a hand into his pocket, pulling out a black collar with gold punched into the leather. He leaned forward and clasped it around your neck, his fingers caressing your soft skin. “you’re a real pet now, pup. one of a kind. gonna learn plenty of new tricks, eh.”You opened your mouth to speak, but your eyes widened as you felt something large prod your entrance. “pups don’t speak,” He said. “they beg.”

Your back arched as he hilted himself in you completely, stretching you in ways you had never felt before. You began to pant, staring up at that wicked grin. “now, don’t get all quiet for me now, pup. beg master to fuck you raw.”

You whimpered again, and leaned up, your lips parting. He hunched over, and pressed his teeth to your shoulder. A sharp moan left your mouth as he bit down, blood oozing from the wound, and staining the dark green couch. Your mind didn't get to focus on the pain as he fucked you at a fast pace, his fingers digging into your thighs, and his ribs rubbing against your chest as you tits bounced against them. You curled your legs around his pelvis, but hissed and retreated when you felt a swat to your ass. That lick of pain only added the the storm brewing in your abdomen, and it didn't take long for you to choke down on your words, fingers digging into the cushion as your orgasm crashed into you. 

You could hear Sans chuckle in your ear, the deep sound sending a shiver down your spine, and making your walls flutter once again. "now ain't that a good bitch." He grabbed some of your hair and yanked your head back. "now lemme see that face again."

* * *

 

Sans led the limping human to a table surrounded by humans. It was the wee hours of morning, most everyone had left who didn’t have buiesness. Sans’ fingers played with the collar again, admiring the transition of leather to skin on his bones, before he dug a hand in his pocket, and pulled out a sheet of paper. There were red stains on it, and it had crumpled during his romp with his pup. He slapped it in front of James, his smile widening when the man looked up sharply from his cards. “got myself a pretty lil whore.” He tugged the human over, cum slipping down her thighs, her body still naked, now bruised and marked with his bites. “ain’t she a catch?” The other men at the table stared at the skeleton, more than one had their eyes lingering over the collared human. “i expect that bundle of lettuce no later than tuesday.”

James stared at the paper for a long moment, before looking up at him and the human. “Didn’t think you could do it,” The old man said with a watery laugh. “You always were full of surprises.”

“wouldn’t say all that.” He began guiding the human away. “now i gotta leave ya and have another round with my new pup.”

He nabbed his coat from an abandoned table, and wrapped it around the human, before guiding her outside. The city lights were waning as the sun began to rise, a few people were already up and moving, but no one questioned why a well dressed man, and a woman with red stains on her face were coming out of a butcher shop before it opened.

No one was stupid enough.

“Hey, Sans?”

“yeah?”

 

“You know you can’t use that bet anymore.” The human said, snuggling deeper into her borrowed coat as a wind blew by. “Everyone will know who I am now.”

“hey, good while it lasted, right?”

“Maybe I can be your wife again, instead of your whore.”

Sans stopped completely, that wicked grin curling onto his teeth as he took of his fedora, hiding both of their faces from the world. “awe, come on pup. you’ll always be both.”

You didn’t get a chance to respond as he kissed you again, this time slow and gentle, like any husband should.

**Author's Note:**

> Wow, this took too long to pump out. My old computer is chugging along, she sounds like those old coffee grinders. XD Anyway, computer problems aside, I really enjoyed writing this lil gem. The type of it fell away from being dominated by sex, and being dominated by that plot twist at the end. I love writing plot twists, but thinking up this one was a bit of a challenge execution wise. 
> 
> Know what isn't a challenge? My tumblr! http://nihilismpastry.tumblr.com/


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